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Molecular Catalysis · 2021 · IF 5.062

Synthesis TS-1 nanozelites via L-lysine assisted route for hydroxylation of Benzene

Mengzhe Li,Xiaohua Shen,Miaoqing Liu,Jianjun Lu

L-lysine is used as a crystallization regulator, and a two-step synthesis method is adopted in a concentrated gel system, which provides a new route to synthesize of nano-sized TS-1 zeolite. The new synthesis strategy was used to successfully synthesize TS-1 zeolite with a particle size less than 100 nm. The rate of crystal nucleation is faster than the crystal growth at the low temperature in the first step. Introduction of L-lysine can prevent crystal growth to form nano-sized TS-1 zeolite at the high temperature in the second step. Meanwhile, L-lysine decrease the pH value of the gel system, which is favorable for Ti atoms to incorporate the TS-1 framework. TS-1 nanozeolite can effectively reduce the diffusion resistance, and nanozeolite has a large specific surface area and high stability. Therefore, TS-1 nanozeolite exhibits the excellent catalytic performance during the hydroxylation of benzene. The conversion of benzene has been greatly improved and the types of by-products are effectively reduced. The conversion of benzene reached 50.2%, and the yield of phenol was 30.8% without by-product benzoquinone. TS-1 nano-zeolite as a catalyst for benzene hydroxylation shows great potential in industrial application.

CAS / MDL: 71-43-2 56-87-1
研究领域: 化学工程 · 材料科学 · 催化化学
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CARBOHYDRATE POLYMERS · 2020 · IF 7.182

Fabrication and characterization of antibacterial epsilon-poly-L-lysine anchored dicarboxyl cellulose beads

Hao Wu,Shuqian Hu,Chunling Nie,Jiahui Zhang,Huafeng Tian,Weicheng Hu,Ting Shen,Jianguo Wang

Pathogens in the food and environment pose a great threat to human health. To solve this problem, we described a novel route to synthesize antibacterial epsilon-poly-L-lysine (EPL) anchored dicarboxyl cellulose beads. Cellulose beads were prepared via a sol-gel transition method and oxidized by sodium periodate and sodium chlorite to form carboxyl groups. EPL was anchored on the beads using carbodiimide mediated amidation. The structure and morphology of beads were characterized by FTIR, XPS, XRD, SEM, and TGA. After dissolution and regeneration, the crystalline form of cellulose is transformed from cellulose I to cellulose II. The thermal degradation temperature of the beads is 200∼300 °C.The samples displayed excellent antimicrobial activity against Staphylococcus aureus , Alicyclobacillus acidoterrestris and Escherichia coli within 12 h. The beads could be biodegraded in soil after 20 days. The biodegradable beads exhibited great potential in food and environmental applications.

研究领域: 材料科学 · 化学 · 生物技术 · 环境科学 · 食品科学
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Polymer Chemistry · 2012 ·Vol. 4 ·期 5 ·1583-1589 · IF 5.321

Vinyl-monomer with lysine side chains for preparing copolymer surfaces with fibrinolytic activity

Zengchao Tang,Dan Li,Xiaoli Liu,Zhaoqiang Wu,Wei Liu,John L. Brash,Hong Chen

A methacrylic monomer containing lysine side groups in which the ε-amino and carboxylic acid groups were protected, was synthesized and copolymerized with 2-hydroxyethyl methacrylate (HEMA) to obtain a series of copolymers (P(HEMA/Lys(P))) of varying composition. After deprotection of the ε-amino and carboxylic acid groups, the corresponding copolymers (P(HEMA/Lys)) were obtained and showed good film-forming properties. P(HEMA/Lys) films were shown to reduce fibrinogen (Fg) adsorption compared to controls and to bind a large quantity of plasminogen from plasma. The plasminogen binding capacity of the copolymer films could be regulated by varying the copolymer composition. Upon activation of adsorbed plasminogen to plasmin, the films were able to rapidly lyse fibrin formed on their surface. These novel copolymers are promising candidates for blood contacting applications.

CAS / MDL: 920-46-7
研究领域: 生物医学工程 · 高分子化学 · 血液学
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FOOD CHEMISTRY · 2019 · IF 5.399

Study of reactions of Nε-(carboxymethyl) lysine with o-benzoquinones by cyclic voltammetry

Yuting Li,Qiaoling Huang,Xiangying Yu,Yujia Liu,Lin Li,Bing Li,Xia Zhang,Sui Chen,Zhan Liu,Xianglong Zhao,Jingjing Ma

The reaction of N ε -(carboxymethyl) lysine (CML) with eight kinds of non-flavonoid o -benzoquinones and five kinds of flavonoid o -benzoquinones were investigated by cyclic voltammetry at pH 5.0, 7.0 and 8.0 and scan rate of 10, 50 and 100 mV/s. The reactivity of o -benzoquinones towards CML is weakened by the electron-donating substituent and strengthened by the electron-withdrawing substituent on the o -benzoquinone rings. The steric hindrance of the substituents on o -benzoquinone rings also weakens the quinone reactivity. Reaction of 4-methylbenzoquinone with CML (38.0 ± 1.3%) was found to be faster than that with l -lysine (31.3 ± 1.5%) and Nα-acetyl- l -lysine (14.5 ± 0.1%) but slower than that with l -cysteine (≥100.0%) and Nα-acetyl- l -cysteine (≥100.0%) at pH 7.0 and scan rate of 10 mV/s. Products obtained by the reaction of CML with o -benzoquinones were found to include a CML-quinone adduct according to the cyclic voltammetry and UPLC-QTOF-MS/MS analysis.

研究领域: 生物化学 · 电化学 · 药物化学
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MACROMOLECULES · 2025 · IF 5.2

l-lysine Efficiently Polymerizes with CO2 under Mild Conditions for Biocompatible Fluorescent Polyurea

Shangzhong Zhang,Yixuan Xu,Panpan Li,Minghui Fan,Dejia Chen,Chengming Wang,Lifeng Yan

Polymerization of CO2 into polyurea under mild pressure and temperature is still a challenge, especially when using diamine from natural feedstocks. Herein, l-lysine is directly used as a diamine without derivatization and protection for capture and copolymerization of CO2 under mild temperatures and pressures (0.1–0.5 MPa, 60–90 °C) with the assistance of superbase 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Water-soluble lysine-polyurea (L-PU) has been synthesized. The weight-average molecular weight of L-PU reaches 3 × 104 g/mol, indicating the efficient reaction of lysine and CO2. In addition, NMR studies confirmed that the unprotected carboxyl acid group (−COOH) in L-PU remains more than 80%, and the polymer may be a candidate to replace nonbiodegradable polyacrylate acid (PAA). The free carboxyl acid group also provides a change to further derivatives of the L-PU. Interestingly, the water-soluble L-PU showed efficient fluorescence performance with quantum yield (QY) up to 20%, which may be attributed to the nonconventional intrinsic fluorescence of nonconjugated aliphatic polyureas containing heteroatoms. It allows the L-PU to be used for cell bioimaging, and in vitro studies reveal that the L-PU is biocompatible and can be efficiently endocytosed by cells with bioimaging ability, indicating that it may be a potential drug delivery system for imaging-guided treatment for cancer tissue.

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Journal of Applied Biomaterials & Functional Materials · 2016 · IF 0.934

Miscibility Evaluation of Poly(L-Lactic Acid)/Poly(Lactic Acid-co-lysine) Blends

Junyan Yao,Shijie Zhang,Wudan Li,Yujie Li

BackgroundThe amorphous poly(lactic acid-co-lysine) (PLL) with hydrophilic reactive groups was synthesized by the condensing copolymerization and the blending miscibility of poly(L-lactic acid) (PLLA) and PLL was investigated.MethodsThe miscibility of PLLA and PLL was evaluated by analyzing the thermal properties, crystallization behaviors, crystal morphologies and mechanical properties of the PLLA/PLL blends.ResultsThe results indicated that amorphous PLL changed the crystallization behaviors and thermal properties of PLLA, decreasing the crystallinity of PLLA in the blends. The amorphous PLL molecule chains in PLLA/PLL blends were able to enter into the lamellars of PLLA spherulites and affect the crystallization behaviors of PLLA, resulting in imperfect, spherulite structures of PLLA. The formation of hydrogen bonds between PLLA molecular chains and PLL molecular chains enabled partial compatibility in this blend system.ConclusionsThe existence of PLL improved the hydrophility of PLLA/PLL blends, led to a higher content of PLL in the PLLA/PLL blend system, and better hydrophilic properties of the blend system. The PLL was partially miscible with the PLLA, and the PLLA/PLL blend with 10 wt% PLL had improved tensile properties.

CAS / MDL: 68-12-2 79-33-4 67-66-3
研究领域: 材料科学 · 高分子化学
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CHINESE JOURNAL OF POLYMER SCIENCE · 2018 ·Vol. 36 ·期 11 ·1239-1250 · IF 2.016

ε-Poly(L-lysine)-based Hydrogels with Fast-acting and Prolonged Antibacterial Activities

Zou Yi-Jie,He Shi-Sheng,Du Jian-Zhong

Bacterial infections and the associated morbidity and mortality due to bacterial pathogens in wounds and medical implants have been increasing as most of current coatings cannot fulfill all the requirements including excellent intrinsically antibacterial activity, low cytotoxicity, and favorable physical properties. Herein, we present a kind of antibacterial hydrogel based on ε -poly(L-lysine) (EPL) grafted carboxymethyl chitosan (CMC- g -EPL) as the inherently antibacterial matrix and the surplus EPL as highly efficient antimicrobial agent. Such hydrogels possess tunable swelling abilities with water absorption percentages of 800%-2000% and modulus varying from 10 kPa to 100 kPa, and exhibit two-stage excellent antibacterial behavior. First, the free EPL can be released from the hydrogel network for quick and highly efficient bacteria killing with 99.99% of efficacy; second, the grafted EPL endows hydrogel matrix with prolonged intrinsically antibacterial activity, especially when most of free EPL is released from the hydrogel. Overall, we provide a new insight for preparing highly effective antibacterial hydrogels.

CAS / MDL: 1310-73-2
研究领域: 生物材料学 · 医学工程 · 感染控制
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2018 · IF 3.44

Fungicidal activity of 10-deacetylbacatin III against Phytophthora capsici via inhibiting lysine biosynthesis

Bi Wang,Shu Xu,Yan Cao,Fei Liu,Xingzeng Zhao,Xu Feng

10-deacetyl-bacatin III (10-DAB) is a natural plant-derived taxane diterpene, whose antimicrobial activity against phytopathogens remains unknown. In this study, we demonstrated the antimicrobial effect of 10-DAB on plant-pathogenic oomycetes . Our results revealed that 10-DAB exhibited significant antimicrobial activities against test oomycetes, especially against Phytophthora capsici , with a median effective concentration (EC 50 ) of 1.46 μg/mL, but had no effect on test fungi. Under 10-DAB treatment, mycelia of P. capsici were contorted with an increased number of top branches, and the production and germination of zoospores were inhibited and delayed, respectively. In addition, 10-DAB had favorable protective and curative activities with control efficacies of 63.90% and 74.81% at 200 μg/mL on detached pepper leaves. Furthermore, 10-DAB caused a significant decrease in soluble protein , lysine, and α, ε-diaminopimelic acid content of P. capsici , which suggested that 10-DAB inhibited the lysine biosynthesis . On the contrary, treatment with exogenous lysine effectively counteracted 10-DAB's inhibition activity on P. capsici . Moreover, relative expression of four key lysine biosynthesis-related genes of P. capsici were decreased upon 10-DAB treatment. Taken together, our findings suggest a lysine biosynthesis inhibiting-dependent antimicrobial activity of 10-DAB against P. capsici , which contributes to accelerating the application of 10-DAB for successful management of phytophthora blight disease in agricultural production.

CAS / MDL: 57837-19-1 32981-86-5
研究领域: 植物病理学 · 分子生物学 · 农业科学
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Journal of Materials Chemistry B · 2016 ·Vol. 4 ·期 8 ·1458-1465 · IF 4.872

Substrate-independent, Schiff base interactions to fabricate lysine-functionalized surfaces with fibrinolytic activity

Xiao-Wen Lu,Wei Liu,Zhao-Qiang Wu,Xin-Hong Xiong,Qi Liu,Wen-Jun Zhan,Hong Chen

Mimicking natural fibrinolytic mechanisms that covalently bind lysine-ligands (free ε-amino and carboxylic groups) onto biomaterial surfaces is an attractive strategy to prevent clot formation on blood contact materials. However, the modification process is typically complicated and limited due to the diversity of biomaterials. Herein, we describe a simple, substrate-independent protocol to prepare a lysine-ligand functionalized layer on biomaterial surfaces. This approach is based on the adsorption and cross-linking of aldehyde-functionalized poly(N-(2,2-dimethoxyethyl)methacrylamide) (APDMEA) and amino-functionalized polymethacryloyl-L-lysine (APMLys) on a variety of substrates, such as polyurethane (PU), polydimethylsiloxane (PDMS), polyvinylchloride (PVC), stainless steel (SS) and cellulose acetate (CA). The lysine-ligand functionalized layer on substrates highly enhanced the specific adsorption of plasminogen from plasma and showed good chemical stability and excellent biocompatibility with L929 cells using the MTT assay. Moreover, for example, after the adsorbed plasminogen was activated and converted into plasmin, the fibrinolytic functionalization of CA was demonstrated using a modified plasma recalcification assay. Collectively, considering the advantages of simplicity, environmental friendliness and substrate-independence, the present study might therefore represent a general approach for the construction of a biointerface with fibrinolytic activity.

CAS / MDL: 920-46-7
研究领域: 生物材料学 · 生物医学工程 · 血液学
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2022 · IF 5.518

L-lysine functionalized Ti3C2Tx coated polyurethane sponge for high-throughput oil–water separation

Zhen-Hui Liu,Qing-Ming Wang,Qiu-Feng Lü,Junxiong Wu

Creating an efficient method that can provide simple, practical and high-throughput separation of oil–water mixtures has proved extremely challenging. Two-dimensional layered Ti 3 C 2 T x MXene material with excellent hydrophilicity has attracted substantial attention for oil–water separation. However, conventional Ti 3 C 2 T x separation membranes are susceptible to contamination by oil due to its relatively high adhesion to oil, hindering its practical applications in high-efficiency oil–water separation. To make Ti 3 C 2 T x have underwater superoleophobicity and low oil adhesion, the surface of Ti 3 C 2 T x can be modified by introducing hydrophilic groups. Herein, L-lysine functionalized Ti 3 C 2 T x (Ti 3 C 2 T x -Ly) was firstly prepared by decorating L-lysine on Ti 3 C 2 T x through electrostatic interaction and hydrogen bonding . A facile dip-coating method is then used to coat polyurethane (PU) sponge with Ti 3 C 2 T x -Ly, obtaining a superhydrophilic/underwater superoleophobic Ti 3 C 2 T x -Ly @PU sponge. Owing to the excellent underwater superoleophobicity resulting from hydrophilic groups (–OH、–NH 3 ) on the surface of Ti 3 C 2 T x -Ly nanosheets and the enlarged interlayer spacing of Ti 3 C 2 T x , the Ti 3 C 2 T x -Ly @PU sponges demonstrated outstanding separation performance for a series of oil–water mixtures. Specifically, the Ti 3 C 2 T x -Ly @PU sponge exhibits low oil adhesion and superhydrophilic (WCA = 0°)/submerged superoleophobic (UOCA > 155°) properties. The Ti 3 C 2 T x -Ly @PU sponges displayed the best separation performance for cyclohexane/water mixture, and the maximum permeation flux is up to 221892 L m –2 h –1 , accompanied by a remarkable separation efficiency of higher than 99.2% after 100 cycles. The permeation flux has exceeded most of the previous reported multifunctional separation membranes. In addition, the Ti 3 C 2 T x -Ly @PU sponge also showed excellent separation performance for high-density oil dichloromethane/water with a separation efficiency over 99.4%. Of note, the Ti 3 C 2 Tx-Ly @PU sponge features excellent chemical stability to corrosive media, such as acidic, alkaline, and high salt solutions, possessing great potential for real-world applications. Furthermore, the as-prepared Ti 3 C 2 T x -Ly @PU sponge exhibits rapid and efficient separation of oil-water mixtures through a fully gravity-driven process, which makes it a good candidate for industrial oil-contaminated water treatment and oil spill clean-up, and also provides new insights into the design and development of functional Ti 3 C 2 T x through L-lysine modification. Therefore, this work reports a facile and promising way to fabricate scalable superhydrophilic/underwater superoleophobic sponge material for highly efficient oil–water separation.

CAS / MDL: 7664-39-3 56-87-1
研究领域: 材料科学 · 环境工程 · 化学工程 · 纳米技术
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Nature Protocols · 2023 ·Vol. 18 ·期 8 ·2600-2623 · IF 14.8

Structural characterization of protein-material interfacial interactions using lysine reactivity profiling-mass spectrometry

Liu Zheyi,Yang Shirui,Zhou Lingqiang,He Min,Bai Yu,Zhao Shan,Wang Fangjun

Understanding how proteins and materials interact is useful for evaluating the safety of biomedical micro/nanomaterials, toxicity estimation and design of nano-drugs and catalytic activity improvement of bio-inorganic functional hybrids. However, characterizing the interfacial molecular details of protein-micro/nanomaterial hybrids remains a great challenge. This protocol describes the lysine reactivity profiling-mass spectrometry strategy for determining which parts of a protein are interacting with the micro/nanomaterials. Lysine residues occur frequently on hydrophilic protein surfaces, and their reactivity is dependent on the accessibility of their amine groups. The accessibility of a lysine residue is lower when it is in contact with another object; allosteric effects resulting from this interaction might reduce or increase the reactivity of remote lysine residues. Lysine reactivity is therefore a useful indicator of protein localization orientation, interaction sequence regions, binding sites and modulated protein structures in the protein-material hybrids. We describe the optimized two-step isotope dimethyl labeling strategy for protein-material hybrids under their native and denaturing conditions in sequence. The comparative quantification results of lysine reactivity are only dependent on the native microenvironments of lysine local structures. We also highlight other critical steps including protein digestion, elution from materials, data processing and interfacial structure analysis. The two-step isotope labeling steps need ~5 h, and the whole protocol including digestion, liquid chromatography-tandem mass spectrometry, data processing and structure analysis needs ~3–5 d.

CAS / MDL: 631-61-8
研究领域: 生物化学 · 材料科学 · 医学工程 · 蛋白质组学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2021 · IF 4.098

A hydrazone-based spectroscopic off-on probe for sensing of basic arginine and lysine

Tianran Wang,Qidan Pang,Zhipu Tong,Hanyue Xiang,Nao Xiao

A simple probe BHN based on naphthol and benzothiazole is reported for detecting of arginine (Arg) and lysine (Lys) with high selectivity and sensitivity. The BHN in aqueous solution upon reacting with Arg or Lys induced a visible color change from colorless to yellow. The probe BHN can also be employed for fluorescence turn-on sensing of Arg and Lys with the limits of detection (LOD) of 5.20 × 10 -2 μM and 3.69 × 10 -2 μM, respectively. The naked eye colorimetric and fluorimetric detecting is lack of sensitive to other common amino acids including Gly, Ala, Ser, Pro, Val, Thr, Cys, Leu, Ile, Asn, Asp, Glu, Gln, Met, His, and Phe. The sensing mechanism has been proposed by pH investigation and 1 H NMR spectra.

研究领域: 分析化学 · 生物化学 · 光谱学
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